Methyl iodide → Methyl 4-chloro-5-fluoropyridine-3-carboxylate

HRID 2369520노트

반응식

HRID 2369520 반응식
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=1[F:11].[CH2:12]1CCN2C(=NCCC2)CC1.IC>C(#N)C>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:12])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=1[F:11]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 114579884-chloro-5-fluoropyridine-3-carboxylic acid

생성물 1

HCID 86695923Methyl 4-chloro-5-fluoropyridine-3-carboxylate수율 65.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 4-chloro-5-fluoronicotinic acid (1.7 g, 9.68 mmol) in acetonitrile (18 mL) was cooled to 0° C. To this solution was added DBU (3.65 mL, 24.21 mmol) dropwise and the resultant solution stirred for 30 min. Iodomethane (3.03 mL, 48.4 mmol) was added dropwise and stirred at room temperature for 12 h. The volatiles were removed completely under reduced pressure and the residue purified via silica gel chromatography using a gradient of ethyl acetate in hexane to afford methyl 4-chloro-5-fluoronicotinate (1.2 g, 6.33 mmol, 65% yield) as a yellow solid. LCMS (ESI) m/e 190.0 [(M+H)+, calcd for C7H6ClFNO2 190.0]; LC/MS retention time (Method F): tR=0.77 min.

후처리

  1. customThe volatiles were removed completely under reduced pressure
  2. customthe residue purified via silica gel chromatography

출처 및 근거

ORD 기록
ord-b77ee4e194224869a196bf85a92c1e77
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703953B2

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